The rapper has never shied away from speaking his mind, which he’s often done in his raps, taking aim at boy bands, pop starlets, political figures and more. Here are Eminem’s five best diss tracks.

“Cleanin’ Out My Closet”

Putting your mother on blast doesn’t seem like the greatest diss, but what’s made Eminem’s work so powerful is his honesty even when it’s brutal and ugly. In “Cleanin’ Out My Closet” off his 2002 album The Eminem Show, the Detroit rapper went after his estranged mother, blaming her for the poor way she raised him and how it negatively affected him. He softened it slightly by apologizing for “cleaning out his closet,” but the track proved that “diss” doesn’t always have to be aimed at a celebrity.

“Doe Rae Me (Hailie’s Revenge)”

Eminem has had a long history beefing with Ja Rule, and his song “Doe Rae Me” took it to the next level. Appearing on Eminem’s 2003 mixtape Straight From the Lab, the track actually began with a sample of Ja rapping before Eminem can be heard cackling in the background. He especially didn’t like how Ja seemed to posture himself after Tupac, a jab he landed on more than one occasion. In “Doe Rae Me,” Eminem rapped, “Ja quit playin’, knock it off, you’re not Tupac/ Don’t hate me, I’m too hot and you’re not.”

“Marshall Mathers”

Eminem’s exhaustion with the pop music scene has made its way into his rhymes again and again. Whether going after Jessica Simpson, Mariah Carey, or, more recently, Iggy Azalea, he hasn’t been quiet about how trite and tried he feels the genre has become. In “Marshall Mathers” off his 2000 album The Marshall Mathers LP, he went after all the fake singers he can’t stand. “I’m anti-Backstreet and Ricky Martin/With instincts to kill N’Sync, don’t get me started/These f—-ing brats can’t sing and Britney’s garbage,” he rapped.

“Mosh”

Before taking down Trump in “Campaign Freestyle,” Eminem had Hillary Clinton and George W. Bush in his sights at different times. In “Mosh Pits” off the 2004 album Encore, he went off on President Bush, rapping, “This coward that we have empowered, this is Bin Laden/Look at his head nodding, how could we allow/Something like this without pumping our fist now.” The song began with children repeating the Pledge of Allegiance with the sound of bombs exploding in the background.

“The Real Slim Shady”

Christina Aguilera got on Eminem’s bad side after she appeared on MTV and began talking about his personal life. He was quick to cut her down to size on his hit single “The Real Slim Shady” off 2000’s The Marshall MathersLP by circulating a few personal rumors of his own. “S—, Christina Aguilera better switch me chairs/So I can sit next to Carson Daly and Fred Durst/And hear ’em argue over who she gave head to first” he rapped at first, before calling her a “b—-” in the next line.